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#$Date: 2023-07-05 05:16:25 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022811.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022811
loop_
_publ_author_name
'Mammadova, Gunay Z.'
'Mertsalov, Dmitriy F.'
'Shchevnikov, Dmitriy M.'
'Grigoriev, Mikhail S.'
'Akkurt, Mehmet'
'Yıldırım, Sema Öztürk'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol tribromide
 (1/1), N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol
 dibromidoiodate (1/1) and
 N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol
 dichloridoiodate (1/1)
;
_journal_coeditor_code           YZ2034
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023005509
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C4 H9 N1 O1, C4 H10 N1 O1 -, Cl2 I -'
_chemical_formula_moiety         'C4 H9 N1 O1, C4 H10 N1 O1 -, Cl2 I -'
_chemical_formula_sum            'C8 H19 Cl2 I N2 O2'
_chemical_formula_weight         373.05
_chemical_name_systematic
'N,N-Dimethylacetamide--1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dichloridoiodate (1/1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.9500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5264(3)
_cell_length_b                   6.7261(2)
_cell_length_c                   10.8124(3)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.14
_cell_measurement_theta_min      3.64
_cell_volume                     736.06(4)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13071
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.200
_diffrn_reflns_theta_min         4.387
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_T_max  0.719
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       fragment
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         1745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0078
_refine_ls_R_factor_gt           0.0078
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0153P)²+0.0381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0216
_refine_ls_wR_factor_ref         0.0216
_reflns_number_gt                1745
_reflns_number_total             1745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2034sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2022811
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.632
_shelx_estimated_absorpt_t_max   0.719
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.500000 0.500000 0.500000 0.01617(2) Uani d 1 . .
Cl Cl1 0.60222(2) 0.500000 0.74187(2) 0.02093(3) Uani d 1 . .
O O1 0.60066(6) 0.000000 0.96603(6) 0.02505(10) Uani d 1 . .
H H1 0.543(3) 0.000000 0.977(3) 0.038 Uiso d 0.5 . .
N N1 0.70175(6) 0.000000 0.81090(6) 0.01741(9) Uani d 1 . .
C C1 0.59151(7) 0.000000 0.84597(6) 0.01742(10) Uani d 1 . .
C C2 0.45979(7) 0.000000 0.74807(8) 0.02291(12) Uani d 1 . .
H H2A 0.390193 -0.021971 0.790959 0.034 Uiso calc 0.5 . .
H H2B 0.457166 -0.106447 0.685527 0.034 Uiso calc 0.5 . .
H H2C 0.445707 0.128418 0.703565 0.034 Uiso calc 0.5 . .
C C3 0.82909(8) 0.000000 0.90856(8) 0.02547(13) Uani d 1 . .
H H3A 0.824028 0.085866 0.980273 0.038 Uiso calc 0.5 . .
H H3B 0.897594 0.049926 0.870861 0.038 Uiso calc 0.5 . .
H H3C 0.851076 -0.135792 0.940046 0.038 Uiso calc 0.5 . .
C C4 0.70493(8) 0.000000 0.67698(7) 0.02212(12) Uani d 1 . .
H H4A 0.622560 0.056849 0.623015 0.033 Uiso calc 0.5 . .
H H4B 0.714477 -0.136724 0.649508 0.033 Uiso calc 0.5 . .
H H4C 0.779897 0.079874 0.668365 0.033 Uiso calc 0.5 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 I1 Cl1 . 5_666 180.0 ?
C1 O1 H1 . . 112(3) ?
C1 N1 C4 . . 123.30(6) ?
C1 N1 C3 . . 119.89(6) ?
C4 N1 C3 . . 116.81(6) ?
O1 C1 N1 . . 117.87(7) ?
O1 C1 C2 . . 121.10(6) ?
N1 C1 C2 . . 121.02(6) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C2 H2A . 6 109.47(11) ?
H2B C2 H2A . 6 123.6 ?
H2C C2 H2A . 6 93.9 ?
C1 C2 H2B . 6 109.5(3) ?
H2A C2 H2B . 6 123.6 ?
H2B C2 H2B . 6 93.9 ?
H2C C2 H2B . 6 17.3 ?
H2A C2 H2B 6 6 109.5 ?
C1 C2 H2C . 6 109.5(2) ?
H2A C2 H2C . 6 93.9 ?
H2B C2 H2C . 6 17.3 ?
H2C C2 H2C . 6 123.6 ?
H2A C2 H2C 6 6 109.5 ?
H2B C2 H2C 6 6 109.5 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N1 C3 H3A . 6 109.5(2) ?
H3A C3 H3A . 6 72.2 ?
H3B C3 H3A . 6 137.5 ?
H3C C3 H3A . 6 40.1 ?
N1 C3 H3B . 6 109.47(14) ?
H3A C3 H3B . 6 137.5 ?
H3B C3 H3B . 6 40.1 ?
H3C C3 H3B . 6 72.2 ?
H3A C3 H3B 6 6 109.5 ?
N1 C3 H3C . 6 109.47(6) ?
H3A C3 H3C . 6 40.1 ?
H3B C3 H3C . 6 72.2 ?
H3C C3 H3C . 6 137.5 ?
H3A C3 H3C 6 6 109.5 ?
H3B C3 H3C 6 6 109.5 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N1 C4 H4A . 6 109.47(15) ?
H4A C4 H4A . 6 45.9 ?
H4B C4 H4A . 6 66.5 ?
H4C C4 H4A . 6 139.6 ?
N1 C4 H4B . 6 109.47(3) ?
H4A C4 H4B . 6 66.5 ?
H4B C4 H4B . 6 139.6 ?
H4C C4 H4B . 6 45.9 ?
H4A C4 H4B 6 6 109.5 ?
N1 C4 H4C . 6 109.47(18) ?
H4A C4 H4C . 6 139.6 ?
H4B C4 H4C . 6 45.9 ?
H4C C4 H4C . 6 66.5 ?
H4A C4 H4C 6 6 109.5 ?
H4B C4 H4C 6 6 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 Cl1 . 2.53980(18) ?
I1 Cl1 5_666 2.53982(18) ?
O1 C1 . 1.2750(8) ?
O1 H1 . 0.64(3) ?
N1 C1 . 1.3161(8) ?
N1 C4 . 1.4576(9) ?
N1 C3 . 1.4608(10) ?
C1 C2 . 1.4955(10) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C2 H2A 6 0.980(5) ?
C2 H2B 6 0.980(15) ?
C2 H2C 6 0.980(10) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C3 H3A 6 0.980(9) ?
C3 H3B 6 0.980(6) ?
C3 H3C 6 0.980(3) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C4 H4A 6 0.980(7) ?
C4 H4B 6 0.9800(17) ?
C4 H4C 6 0.980(8) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O1 5_657 0.64(3) 1.79(3) 2.4261(11) 170(4) yes
C2 H2A Cl1 3_445 0.98 2.93 3.7461(8) 140.9 yes
C2 H2A O1 5_657 0.98 2.61 3.3230(9) 130.0 yes
C2 H2C Cl1 . 0.98 2.96 3.6902(3) 132.2 yes
C3 H3A Cl1 7_657 0.98 2.95 3.6479(9) 129.4 yes
C3 H3B Cl1 3_545 0.98 2.89 3.7897(8) 153.2 yes
C3 H3C O1 7_647 0.98 2.65 3.6256(4) 176.3 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 O1 . . . . 180.000000 ?
C3 N1 C1 O1 . . . . 0.000000 ?
C4 N1 C1 C2 . . . . 0.000000 ?
C3 N1 C1 C2 . . . . 180.000000 ?

_cod_database_fobs_code 2022811
